2-Nitrobenzenesulfonyl chloride → HCID 22722449, compound

HRID 1977965Notes

Reaction equation

HRID 1977965 reaction equation
[OH2:1].[C:2]1([OH:10])[CH:9]=[C:7](C)[CH:6]=[C:4](O)[CH:3]=1.[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20](Cl)(=[O:22])=[O:21])([O-:13])=[O:12]>C(OCC)C.C([O-])(O)=O.[Na+].O>[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20]([O:10][C:2]1[CH:3]=[CH:4][CH:6]=[CH:7][C:9]=1[OH:1])(=[O:22])=[O:21])([O-:13])=[O:12]

Participants

6

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 22722449HCID 22722449, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of orcinol monohydrate (4.32 g, 30.2 mmol) and 2-nitrobenzenesulfonyl chloride (6.65 g, 30.0 mmol) in diethyl ether (100 mL) and saturated NaHCO3 (100 mL) was stirred at ambient temperature for 36 h. The reaction mixture was diluted with water (100 mL) and extracted into 10% tetrahydrofuran/ethyl acetate, dried (MgSO4), and concentrated. The residue was diluted with diethyl ether (150 mL) and the resulting disulfonated product (1.6 g) removed by filtration. The filtrate was concentrated and purified by flash chromatography (3:97 to 10:90 diethyl ether/dichloromethane) to give 5.67 g (61%) of the title compound as an oil. 1H-NMR (300 MHz, CDCl3) δ7.99 (dd, 1H, J=7, 2 Hz), 7.79-7.86 (m, 2H), 7.65-7.73 (m, 1H), 6.60-6.61 (m, 1H), 6.58-6.59 (m, 1H), 6.50-6.51 (m, 1H), 5.32 (s, 1H), 2.25 (s, 3H).

Workup

  1. extractionextracted into 10% tetrahydrofuran/ethyl acetate
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. additionThe residue was diluted with diethyl ether (150 mL)
  5. customthe resulting disulfonated product (1.6 g) removed by filtration
  6. concentrationThe filtrate was concentrated
  7. custompurified by flash chromatography (3:97 to 10:90 diethyl ether/dichloromethane)

Sources & evidence

ORD record
ord-89fd23b2316b4c5dac058fc62b55b6b4
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

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